Red
Cloud and American Horse. Probably one of a series of David
Barry photos taken during Buffalo Bill's Wild West Show's
stint at Madison Square Gardens in 1897.
Another
from this series, with a Mr Goodwin standing between RC
and AH:

A
photo by Felix Flying Hawk, taken around 1905:

I'm
fairly sure I've seen another photo like the one below,
which I presume was taken in the early 1900s:

—
Grahame Wood
The
image [above] of the mounted man, captioned "Chief
Red Cloud (Sioux)", does not show Jack, but James Red
Cloud, Jack's son (I guess late 1920s/1930s). —
Hans Karkheck

I
saw a copy of this years ago from Don Diessner's collection
( he wrote THERE ARE NO INDIANS LEFT BUT ME! SITTING BULL'S
STORY-Upton and Sons 1993) and was told Red Cloud and Sitting
Bull were in it. Red Cloud is wearing trousers, but not
the fur hat and capote you remember. I'm not so sure the
man with blanket and fan is Sitting Bull. Could be, though.
Princeton doesn't have any information on the identity.

—
Bob/buffaloman
I
am most positive that the man with blanket & fan &
hat is NOT Sitting Bull. However, this individual could
be ( and I am nearly convinced) He Dog. He obviously had
a special liking for fans, ties and hats, as a number of
later portraits of him would reveal. —
Hans Karkheck
This
is not Red Cloud but his son Jack in a 1909 photo by German
photographer Frederick Weygold. I do like this picture a
lot, because you can imagine how Red Cloud must have looked
like in his warrior days:

—
Dietmar Schulte-Möhring
According
to Goodyear's book on Red Cloud's portraits, Frederick Weygold
visited the Pine Ridge Reservation in July 1909.
Gus
Trager was active in Crawford and Chadron, Nebraska, from
1889 to 1892. Incidentally, this photographer's name was
never George, despite its publication in recent articles
that way. I have tracked him through hundreds of documents,
including newspaper accounts, county records, census records,
etc. Not once is he ever referred to as George -- always
as Gustavaus or Gus. —
Ephriam Dickson
Another
Red Cloud photo:

Dated circa 1900

The following publications contain information about Red Cloud:
Article: "Slaughter at Fort Phil Kearney" by J. P. Dunn, Jr. • Real West • Vol. VII, No. 37 • September 1964.
Article: "Strange Death of 'Lonesome' Charley Reynolds" by Fred Harrison • Like so many other young men, Reynolds would have crawled through hell on his hands and knees had Elizabeth Custer asked, but what she wanted of him did her no discredit—and perceptive Lonesome Charley got the message. • Golden West Magazine • November 1968.
Book: Red Cloud: Warrior-Statesman of the Lakota Sioux by Robert W. Larson • University of Oklahoma Press • 1997.